Method for producing transesterified oil / fat composition, method for producing oil / fat composition, method for improving absorption properties of c13-c15 fatty acid, method of improving bioavailability of c13-c15 fatty acid, and bioavailability improver

Abstract

A method for producing a transesterified oil / fat composition (excluding hard butter and oil / fat for puff pastry margarine), said method comprising a step for subjecting a starting material oil / fat that contains a triglyceride, which is composed of a C13-C15 fatty acid, and an oil / fat other than said triglyceride to transesterification to obtain a transesterified oil / fat composition, wherein the C13-C15 fatty acid constitutes at least 3 mass% but less than 100 mass% of the total fatty acids in the transesterified oil / fat composition.

Description

Method for producing transesterified fat compositions, method for producing fat compositions, method for improving the absorption of fatty acids having 13 to 15 carbon atoms, method for improving the bioavailability of fatty acids having 13 to 15 carbon atoms, and bioavailability improving agent.

[0001] The present invention relates to a method for producing a transesterified oil composition, a method for producing an oil composition, a method for improving the absorption of fatty acids having 13 to 15 carbon atoms, a method for improving the bioavailability of fatty acids having 13 to 15 carbon atoms, and a bioavailability improving agent.

[0002] Patent documents 1 to 7 describe techniques for obtaining oil and fat compositions with desired properties. Patent document 1 (Japanese Patent Publication No. 55-61780) describes a method for producing a butter flavor with a good, strong butter aroma using inexpensive raw materials that are abundant in nature (page 1, left column), and describes a method for producing a butter flavor by adding a lipolytic enzyme to oil and fat to decompose it, and then adding lipoxygenase to decompose it further (Claim 1). The same document also describes a transesterification process in which beef tallow and several types of specific triglycerides were mixed (Example 2).

[0003] Patent Document 2 (Japanese Patent Publication No. 2001-40386) describes a fat and oil composition containing specific amounts of triglycerides, diglycerides, monoglycerides, and free fatty acids, and further containing specific amounts of ω3 unsaturated acyl groups and monoene acyl groups in the acyl groups constituting the diglycerides (Claim 1). Such a fat and oil composition is said to be resistant to oxidation, fluid, and has excellent flavor, and can effectively exhibit the physiological activity of ω3 unsaturated fatty acids (Paragraph 0045).

[0004] Patent Document 3 (Japanese Patent Publication No. 2020-510607) describes a manufactured article comprising a composition or food, wherein the composition or food comprises carbohydrates, proteins, and fats, and at least 30% by weight of the food consists of fats of a specific composition (Claim 1), with triglycerides being given as an example of the form of the fat (Claim 2).

[0005] Patent Document 4 (Japanese Patent Laid-Open No. 63-246320) describes a composition suitable for transporting an active ingredient containing vesicles in a carrier acceptable for a drug, the composition containing vesicles, an active ingredient mixed with a triglyceride, and a capsule agent containing a phospholipid substance (Claim 1), and it is exemplified that trilaurin or trimyristin is included as the triglyceride (Claim 12).

[0006] Patent Document 5 (Japanese Patent Laid-Open No. 63-287720) describes a pharmaceutical preparation suitable for use as a powder, a capsule agent, or an aqueous solution composed of drug granules and a coating applied to the surface thereof, the coating consisting of at least three layers, the innermost layer being a layer of substantially pure fat, the intermediate layer being a layer of a mixture of fat and a polymer, and the outermost layer being a layer of substantially pure fat (Claim 1), and it is described that the fat is a triglyceride of a fatty acid, such as trimyristin (Claims 2, 5).

[0007] Patent Document 6 (Japanese Patent Translation Laid-Open No. 2023-538610) describes a method for enhancing and / or boosting mood, reducing anxiety and / or pain, treating depression, treating major depressive disorder, or treating seasonal affective disorder: administering an effective amount of a C15:0 fatty acid or a pharmaceutically acceptable salt thereof to a patient in need thereof in a pharmaceutical composition, a dietary supplement, or a food (Claim 1), and pentadecanoic acid is described as the C15:0 fatty acid (Claim 5).

[0008] Further, Patent Document 7 (Japanese Patent Laid-Open No. 2023-99029) describes a supplement for treating inflammation containing at least one odd-chain saturated fatty acid or a pharmaceutically acceptable salt thereof, at least one odd-chain saturated fatty acid being selected from the group consisting of C15:0, C17:0, and combinations thereof (Claim 1), and pentadecanoic acid is described as at least one odd-chain saturated fatty acid (Claim 4).

[0009] Japanese Patent Publication No. 55-61780, Japanese Patent Publication No. 2001-40386, Japanese Patent Publication No. 2020-510607, Japanese Patent Publication No. 63-246320, Japanese Patent Publication No. 63-287720, Japanese Patent Publication No. 2023-538610, Japanese Patent Publication No. 2023-99029

[0010] Fatty acids with 13 to 15 carbon atoms (for example, myristic acid) are known to have various health benefits. Therefore, when ingesting such fatty acids as supplements, it is necessary that they be absorbed efficiently. Specifically, it is important to efficiently deliver fatty acids with 13 to 15 carbon atoms into the circulating blood and improve their bioavailability. On the other hand, the technology described in the aforementioned patent document had room for improvement in this respect.

[0011] This invention provides a novel technology for improving the bioavailability of fatty acids having 13 to 15 carbon atoms.

[0012] Through the inventors' research, it has been newly discovered that when ingesting fatty acids with 13 to 15 carbon atoms, the bioavailability of the fatty acids can be improved by transesterifying triglycerides composed of fatty acids with 13 to 15 carbon atoms with other oils and fats to produce transesterified oil, and then ingesting the resulting transesterified oil, compared to ingesting them as free fatty acids.

[0013] The present invention provides the following manufacturing methods, methods, and agents: [1] A method for producing a transesterified fat composition (excluding fats and oils for hard butter and puff pastry margarine), comprising the step of transesterifying a raw oil containing a triglyceride composed of fatty acids having 13 to 15 carbon atoms and a fat other than the triglyceride to obtain a transesterified fat composition, wherein the transesterified fat composition contains 3% by mass or more and less than 100% by mass of fatty acids having 13 to 15 carbon atoms in the total fatty acids. [2] The manufacturing method according to [1], wherein the fat other than the triglyceride is a vegetable oil. [3] The manufacturing method according to [1] or [2], wherein the triglyceride composed of fatty acids having 13 to 15 carbon atoms is glyceryl tritetradecanoate. [4] The manufacturing method according to any one of [1] to [3], wherein the content of C20:5 fatty acids in the total fatty acids of the transesterified fat composition is 20% by mass or less. [5] The manufacturing method according to any one of [1] to [4], wherein the transesterification in the step of obtaining the transesterified oil composition is random transesterification. [6] The manufacturing method according to any one of [1] to [5], which is a method for producing a transesterified oil composition for supplements. [7] The manufacturing method according to any one of [1] to [6], which is a method for producing a transesterified oil composition for use as a bioavailability enhancer for fatty acids having 13 to 15 carbon atoms. [8] A method for producing an oil composition, comprising the step of obtaining a transesterified oil composition by the manufacturing method for a transesterified oil composition according to any one of [1] to [7]. [9] The manufacturing method according to [8], further comprising the step of mixing the transesterified oil composition with an oil other than the transesterified oil composition.

[10] A method for improving the absorption of fatty acids having 13 to 15 carbon atoms, comprising the step of having an animal ingest a transesterified oil composition produced by the manufacturing method according to any one of [1] to [7].

[11] A method for improving the bioavailability of a fatty acid having 13 to 15 carbon atoms, comprising the step of having an animal ingest a transesterified oil composition produced by any one of the manufacturing methods described in [1] to [7].

[12] A bioavailability enhancer comprising, as an active ingredient, a transesterified oil composition made from a triglyceride composed of fatty acids having 13 to 15 carbon atoms and oils other than the triglyceride as raw materials, wherein the total fatty acids of the transesterified oil composition contain 3% by mass or more and less than 100% by mass of fatty acids having 13 to 15 carbon atoms.

[13] The bioavailability enhancer according to

[12] , which is an oral composition.

[0014] According to the present invention, a new technology can be provided for improving the bioavailability of fatty acids having 13 to 15 carbon atoms.

[0015] This figure shows the measurement results of myristic acid concentration in plasma in the example. This figure shows the measurement results of myristic acid concentration in plasma in the example. This figure shows the measurement results of the area under the curve (AUC) of myristic acid in the blood concentration in the example. This figure shows the measurement results of the AUC of myristic acid in the example. This figure shows the measurement results of the myristic acid excretion rate in the example. This figure shows the measurement results of the myristic acid excretion rate in the example.

[0016] Embodiments of the present invention will be described below. In these embodiments, the composition may contain each component individually or in combination of two or more components. In this specification, the "~" indicating a numerical range represents "greater than or equal to" and "less than or equal to," including both of the numerical values ​​at either end. Furthermore, when upper and lower limits of a numerical range are indicated, the upper and lower limits may be combined as appropriate, and the resulting numerical range is also disclosed.

[0017] (Method for producing a transesterified fat composition) In this embodiment, the method for producing a transesterified fat composition (excluding fats for hard butter and puff pastry margarine) includes the following step 10. (Step 10) A step of transesterifying a raw oil containing triglycerides composed of fatty acids having 13 to 15 carbon atoms and fats other than triglycerides to obtain a transesterified fat composition. The transesterified fat composition obtained in this embodiment contains 3% by mass or more and less than 100% by mass of fatty acids having 13 to 15 carbon atoms in its total fatty acids.

[0018] In this embodiment, the method for producing the transesterified oil composition includes the above step 10, and because the content of fatty acids with 13 to 15 carbon atoms in the transesterified oil composition (hereinafter also referred to as "C13-C15 fatty acids") is within a specific range, the absorption rate of C13-C15 fatty acids in the circulating blood can be improved. Furthermore, by improving the efficiency of C13-C15 fatty acids reaching the circulating blood, it is possible to improve bioavailability. In addition, the method for producing the transesterified oil composition of this embodiment can reduce the excretion rate of C13-C15 fatty acids. Here, if we define (amount of C13-C15 fatty acid intake (100%)) - (excretion rate of C13-C15 fatty acids) = absorption rate of C13-C15 fatty acids, then it can be said that the absorption rate of C13-C15 fatty acids can be improved by reducing the excretion rate of C13-C15 fatty acids.

[0019] The raw material oils and fats in step 10 include triglycerides composed of C13-C15 fatty acids and oils and fats other than the above triglycerides. Of these, the triglycerides may be composed of C13-C15 fatty acids, and preferably composed of C13-C15 saturated fatty acids. The triglycerides may be triglycerides composed of a single fatty acid such as tritridecanoate glyceryl, tritetradecanoate glyceryl, or tripentadecanate glyceryl, or they may be triglycerides composed of mixed fatty acids with 13 to 15 carbon atoms. From the viewpoint of availability, the triglycerides are preferably at least one triglyceride selected from the group consisting of tritridecanoate glyceryl, tritetradecanoate glyceryl, and tripentadecanate glyceryl, and more preferably tritetradecanoate glyceryl.

[0020] Examples of fats and oils other than triglycerides include animal fats and non-animal fats. Examples of animal fats include natural animal fats such as beef tallow, pork tallow, chicken tallow, milk fat, and fish oil; and synthetic fats of animal origin such as EPA (eicosapentaenoic acid) triglyceride and DHA (docosahexaenoic acid) triglyceride. Examples of non-animal fats include vegetable oils and algal oils. Specific examples of vegetable oils include natural vegetable oils such as rapeseed oil, soybean oil, corn oil, sesame oil, coconut oil, palm oil, palm kernel oil, rice oil, cottonseed oil, safflower oil, sunflower oil, olive oil, linseed oil, perilla oil, peanut oil, sal fat, cocoa butter, and shea butter; and synthetic fats of plant origin such as MCT. Examples of algal oils include Euglena oil. Furthermore, oils and fats other than triglycerides may be processed oils such as transesterified oils, fractionated oils, or hydrogenated oils of the above-mentioned animal oils and fats or non-animal oils.

[0021] The fats and oils other than triglycerides are preferably non-animal fats and oils, more preferably one or more selected from the group consisting of vegetable oils and processed vegetable oils and oils, even more preferably vegetable oils, even more preferably one or more selected from the group consisting of rapeseed oil, soybean oil, and corn oil, and even more preferably rapeseed oil. This makes it possible to obtain more desirable physical properties as a transesterified fat. Furthermore, in terms of obtaining more desirable physical properties, the fats and oils other than triglycerides are preferably vegetable oils in which the content of fatty acids with 16 carbon atoms in the total fatty acids is 10% by mass or less, more preferably 9% by mass or less, and even more preferably 7% by mass or less.

[0022] In step 10, transesterification can be carried out by known methods. The transesterification method may be random transesterification or specific transesterification of the fatty acids bonded to the 1st and 3rd positions of glycerol. Random transesterification is preferred in that it more stably improves the bioavailability of C13-C15 fatty acids. Examples of catalysts used for transesterification include chemical catalysts such as sodium methoxide and enzyme catalysts such as lipase.

[0023] The transesterified oil composition can be produced, for example, by the following method. Specifically, 0.3 parts by mass of sodium methoxide is added as a catalyst to 100 parts by mass of raw oil, which is a mixture of triglycerides composed of fatty acids with 13 to 15 carbon atoms and oils other than triglycerides, and a random transesterification reaction is carried out for 60 minutes while stirring at 80°C and a vacuum of 2.0 kPa. After the random transesterification reaction, the catalyst is removed by washing with water. After washing with water, decolorization is performed using activated clay, and then deodorization is performed to obtain the transesterified oil composition. Furthermore, in step 10, the content of C13-C15 fatty acids in the total fatty acids of the product, the transesterified oil composition, can be adjusted, for example, by adjusting the type and blend of raw oils.

[0024] Next, the fatty acid composition of the transesterified oil composition obtained in step 10 will be described. In the transesterified oil composition obtained in step 10, the content of C13-C15 fatty acids in the total fatty acids is 3% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 12% by mass or more, even more preferably 15% by mass or more, even more preferably 20% by mass or more, even more preferably 30% by mass or more, even more preferably 40% by mass or more, and even more preferably 45% by mass or more. This makes it possible to more reliably improve the absorption efficiency of C13-C15 fatty acids. Also, in the transesterified oil composition obtained in step 10, the content of C13-C15 fatty acids in the total fatty acids is 12% by mass or more, preferably 15% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, even more preferably 40% by mass or more, and even more preferably 45% by mass or more. This makes it possible to more reliably improve the absorption efficiency of C13-C15 fatty acids. In the transesterified fat composition, the content of C13-C15 fatty acids in the total fatty acids is less than 100% by mass. To obtain more favorable processing suitability, it is preferably 98% by mass or less, more preferably 95% by mass or less, even more preferably 90% by mass or less, and even more preferably 85% by mass or less. The content of each fatty acid in the total fatty acids in the transesterified fat composition or the fat composition described later refers to the content expressed as a mass percentage calculated using the molecular weight of the fatty acid from the mass percentage derived from the area value obtained by gas chromatography (GC) as described in the Examples section.

[0025] In the total fatty acids of the transesterified oil composition, the content of fatty acids having 12 carbon atoms is preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, even more preferably 1% by mass or less, and even more preferably 0% by mass. This allows for a more stable acquisition of the bioavailability improvement effect. Alternatively, the content of fatty acids having 12 carbon atoms in the total fatty acids of the transesterified oil composition may be, for example, 0% by mass or more, or 0.1% by mass or more.

[0026] In the total fatty acids of the transesterified oil composition, the content of carbon-12 fatty acids is preferably 2.5 or less by mass ratio to the content of C13-C15 fatty acids, more preferably 2.0 or less, even more preferably 1.5 or less, even more preferably 1.0 or less, even more preferably 0.5 or less, and even more preferably 0. This allows for a more stable acquisition of the bioavailability improvement effect. Furthermore, the above mass ratio ((carbon-12 fatty acids) / (C13-C15 fatty acids)) may be, for example, 0 or more or 0.1 or more.

[0027] In the total fatty acids of the transesterified oil composition, the content of fatty acids having 16 carbon atoms is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and even more preferably 0.6% by mass or more. This allows for obtaining more favorable processing suitability. Similarly, in the total fatty acids of the transesterified oil composition, the content of fatty acids having 16 carbon atoms is preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 12% by mass or less, even more preferably 10% by mass or less, and even more preferably 8% by mass or less.

[0028] The content of unsaturated fatty acids having 18 carbon atoms in the total fatty acids of the transesterified oil composition is preferably 5% by mass or more, more preferably 8% by mass or more, even more preferably 10% by mass or more, even more preferably 13% by mass or more, and even more preferably 15% by mass or more. This makes it possible to obtain more favorable processing properties. Alternatively, the content of unsaturated fatty acids having 18 carbon atoms in the total fatty acids of the transesterified oil composition may be, for example, 85% by mass or less, 82% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 55% by mass or less, or 50% by mass or less.

[0029] In the total fatty acids of the transesterified oil composition, the content of C20:5 fatty acids, i.e., EPA (eicosapentaenoic acid), is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, even more preferably 1% by mass or less, and even more preferably 0.5% by mass or less. This makes it possible to achieve better storage stability. In addition, the content of EPA in the total fatty acids of the transesterified oil composition may be, for example, 0% by mass or more, or 0.1% by mass or more.

[0030] The total content of EPA and C22:6 fatty acids, i.e., DHA (docosahexaenoic acid), in the total fatty acids of the transesterified oil composition is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, even more preferably 2% by mass or less, even more preferably 1% by mass or less, and even more preferably 0.5% by mass or less. This makes it possible to achieve better storage stability. In addition, the total content of EPA and DHA in the total fatty acids of the transesterified oil composition may be, for example, 0% by mass or more, or 0.1% by mass or more.

[0031] The content of polyunsaturated fatty acids in the total fatty acids of the transesterified oil composition is preferably 1% by mass or more, more preferably 2% by mass or more, even more preferably 3% by mass or more, and even more preferably 5% by mass or more. This makes it possible to obtain more favorable processing suitability. Similarly, the content of polyunsaturated fatty acids in the total fatty acids of the oil composition is preferably 70% by mass or less, more preferably 60% by mass or less, even more preferably 55% by mass or less, even more preferably 50% by mass or less, even more preferably 40% by mass or less, even more preferably 30% by mass or less, and even more preferably 25% by mass or less.

[0032] In this embodiment, the method for producing the transesterified oil composition includes step 10 described above, and since the content of C13-C15 fatty acids in the total fatty acids of the transesterified oil composition is within the range described above, a transesterified oil composition with excellent bioavailability of C13-C15 fatty acids can be obtained. For this reason, the method for producing the transesterified oil composition may be, for example, a method for producing a transesterified oil composition used as a bioavailability enhancer for C13-C15 fatty acids. Alternatively, the method for producing the transesterified oil composition may be, for example, a method for producing a transesterified oil composition for supplements.

[0033] (Method for producing the oil and fat composition) In this embodiment, the method for producing the oil and fat composition includes the step of obtaining a transesterified oil and fat composition by the method for producing the transesterified oil and fat composition in this embodiment described above.

[0034] In this embodiment, since the method for producing the oil and fat composition includes the step of obtaining the above-mentioned transesterified oil and fat composition, an oil and fat composition with excellent bioavailability of C13-C15 fatty acids can be obtained. The oil and fat composition obtained in this embodiment may consist of the transesterified oil and fat composition, or it may contain oils and fats other than the transesterified oil and fat composition.

[0035] The method for producing the oil and fat composition may further include at least one of the following steps 20 and 30. Furthermore, the method for producing the transesterified oil and fat composition described above may further include step 30. (Step 20) A step of mixing the transesterified oil and fat composition with oils and fats other than the transesterified oil and fat composition (hereinafter also referred to as "other oils and fats"). (Step 30) A step of reacting C13-C15 fatty acids and glycerin to obtain the above triglycerides. Each of these steps will be described below.

[0036] (Step 20) In step 20, the transesterified oil composition is mixed with other oils. By further including step 20, the oil composition can be imparted with further desired properties and effects.

[0037] The content of the transesterified oil composition in the oil composition is, for example, more than 0% by mass and 100% by mass or less, relative to the entire oil composition. In order to more reliably improve the bioavailability of C13-C15 fatty acids, the content of the transesterified oil composition in the oil composition is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, even more preferably 30% by mass or more, and even more preferably 40% by mass or more, relative to the entire oil composition. Furthermore, when the method for producing the oil composition includes step 20, the content of the transesterified oil composition in the oil composition may be less than 100% by mass, 99% by mass or less, 95% by mass or less, or 90% by mass or less, relative to the entire oil composition.

[0038] In step 20, the other fats and oils specifically refer to other edible fats and oils. Examples of other edible fats and oils include rapeseed oil, olive oil, sesame oil, soybean oil, flaxseed oil, corn oil, sunflower oil, safflower oil, cottonseed oil, rice oil, peanut oil, perilla oil, palm oil, medium-chain triglycerides (MCT), DHA triglycerides, EPA triglycerides, algal oil, and processed fats and oils obtained by fractionation, hydrogenation, transesterification, etc. Preferably, the other edible fats and oils include one or more selected from the group consisting of rapeseed oil, olive oil, sesame oil, soybean oil, flaxseed oil, and medium-chain triglycerides, and more preferably, one or more selected from the group consisting of rapeseed oil, olive oil, and sesame oil. This makes it possible to easily impart desired flavors and physical properties to oil and fat compositions. Here, MCT refers to a medium-chain fatty acid, specifically a triglyceride composed of saturated fatty acids having 8 to 10 carbon atoms.

[0039] The content of other oils in the oil composition can specifically be the remainder after subtracting the total content of components other than other oils in the oil composition. Furthermore, when the oil composition contains other oils, the content of other oils in the oil composition may be, for example, more than 0% by mass and less than 100% by mass, 1% to 90% by mass, 2% to 85% by mass, 5% to 80% by mass, 10% to 75% by mass, 20% to 70% by mass, or 30% to 65% by mass.

[0040] The content of C13-C15 fatty acids in the total fatty acids of the oil and fat composition is preferably 0.5% by mass or more, more preferably 1% by mass or more, even more preferably 3% by mass or more, even more preferably 5% by mass or more, even more preferably 8% by mass or more, and even more preferably 10% by mass or more. This allows for a more efficient improvement of the bioavailability of C13-C15 fatty acids. The content of C13-C15 fatty acids in the total fatty acids of the oil and fat composition is less than 100% by mass, and from the viewpoint of imparting desired flavor and physical properties, it is preferably 98% by mass or less, more preferably 95% by mass or less, even more preferably 90% by mass or less, even more preferably 85% by mass or less, and even more preferably 80% by mass or less.

[0041] The EPA content in the total fatty acids of the oil and fat composition is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, even more preferably 1% by mass or less, and even more preferably 0.5% by mass or less. This allows for a more stable acquisition of the bioavailability improvement effect. Alternatively, the EPA content in the total fatty acids of the oil and fat composition may be, for example, 0% by mass or more, or 0.1% by mass or more.

[0042] (Step 30) In Step 30, C13-C15 fatty acids and glycerin are reacted to obtain the above triglyceride. Step 30 is specifically carried out before Step 10. In Step 30, commercially available products can be used as both the C13-C15 fatty acids and glycerin. The C13-C15 fatty acids are, for example, saturated fatty acids having 13 to 15 carbon atoms, and more specifically, are one or more fatty acids selected from the group consisting of tridecanoic acid, tetradecanoic acid (myristic acid), and pentadecanoic acid, preferably tetradecanoic acid.

[0043] Step 30 can be carried out by a conventional method. The triglyceride obtained in Step 30 may be a triglyceride consisting of a single fatty acid such as glyceryl tritridecanoate, glyceryl tritetradecanoate, glyceryl tripentadecanoate, etc., or may be a triglyceride consisting of a mixed fatty acid having 13 to 15 carbon atoms. From the viewpoint of ease of availability, the triglyceride obtained in Step 30 is preferably at least one triglyceride selected from the group consisting of glyceryl tritridecanoate, glyceryl tritetradecanoate, and glyceryl tripentadecanoate, and more preferably glyceryl tritetradecanoate.

[0044] The transesterified oil and fat composition obtained in this embodiment and the oil and fat composition containing the same may be used as they are or as production raw materials, and can be preferably used, for example, in the production of oral compositions such as supplements. Here, when the transesterified oil and fat composition or the oil and fat composition containing the same is used as it is, they are specifically not hard butter (oil for chocolate). Also, when the transesterified oil and fat composition or the oil and fat composition containing the same is used as a production raw material for food, they are specifically not oil for puff pastry margarine.

[0045] (Bioavailability Enhancer) In this embodiment, the bioavailability enhancer contains as an active ingredient a transesterified oil composition made from triglycerides composed of C13-C15 fatty acids and oils other than the above triglycerides as raw materials, and contains 3% by mass or more and less than 100% by mass of fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified oil composition. Specifically, the transesterified oil composition is obtained by the manufacturing method of this embodiment described above. Because it contains such a transesterified oil composition as an active ingredient, the bioavailability enhancer has excellent absorption efficiency of C13-C15 fatty acids in the circulating blood and has an excellent bioavailability enhancing effect of C13-C15 fatty acids.

[0046] The bioavailability enhancer is preferably an oral composition. This makes it easier for the target to take. The oral composition is preferably a food or beverage composition or a pharmaceutical composition.

[0047] Specific examples of food and beverage compositions include oil and fat compositions, confectionery (snack foods such as potato chips, baked goods such as cookies and cakes, Japanese sweets, chocolate, candy, pudding, jelly, ice cream, gummies, gum, etc.), bread (sweet bread, savory bread, croissants, Danish pastries, etc.), noodles (ramen, udon, pasta, etc.), rice products (rice balls, porridge, fried rice, etc.), cereal foods (cornflakes, oatmeal, etc.), dairy products (cheese, yogurt, etc.), processed meat products (ham, sausage, etc.), processed seafood products (fish cakes, fish sausage, etc.), and seasonings. Examples include mayonnaise, sauces, dressings, soups (miso soup, vegetable soup, etc.), processed foods and beverages (stews, fried foods, grilled foods, curry, etc.), premixed flours (okonomiyaki flour, fried chicken flour, confectionery mixes, etc.), solid roux (curry roux, etc.), beverages (alcoholic beverages such as beer, soft drinks such as sports drinks, lactic acid drinks, or vegetable juices, tea such as black tea, coffee, etc.), foods and beverages for elderly care (liquid foods, etc.), health foods, functional foods, foods for specified health uses, foods with functional claims, nutritional functional foods, nutritional supplements, supplements, protein, and animal feed.

[0048] Among these, as the dosage forms of the supplement, tablets (plain tablets, sugar-coated tablets, effervescent tablets, film-coated tablets, chewable tablets, troches, etc.), pills, capsules (hard capsules, soft capsules, seamless capsules, etc.), granules, powders, liquids, syrups, jellies, candies, gummies, etc. can be mentioned. Also, from the viewpoint of excellent portability and ease of ingestion in the subject, the bioavailability enhancer is preferably a solid preparation.

[0049] As the pharmaceutical composition, pharmaceuticals and quasi-drugs can be mentioned. The pharmaceutical composition includes an ester-exchanged oil and fat composition, and may appropriately contain additives and the like usually used in pharmaceutical compositions. As the dosage form of the pharmaceutical composition, for example, oral dosage forms such as tablets (plain tablets, sugar-coated tablets, effervescent tablets, film-coated tablets, chewable tablets, troches, etc.), pills, capsules (hard capsules, soft capsules, seamless capsules, etc.), granules, powders, liquids, syrups, jellies, candies, gummies, etc.; parenteral dosage forms such as injections, drip infusions, suppositories, etc.; and external preparations such as ointments, plasters, etc. can be mentioned.

[0050] The content of the ester-exchanged oil and fat composition in the bioavailability enhancer is preferably 3% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, still more preferably 20% by mass or more, still more preferably 30% by mass or more, still more preferably 40% by mass or more, still more preferably 50% by mass or more, still more preferably 60% by mass or more, still more preferably 65% by mass or more with respect to the whole bioavailability enhancer. Thereby, while suppressing the intake amount of the bioavailability enhancer, C13-C15 can be efficiently absorbed. Also, from the viewpoint of the manufacturing suitability of the bioavailability enhancer, the content of the ester-exchanged oil and fat composition in the bioavailability enhancer is 100% by mass or less, preferably 95% by mass or less, more preferably 90% by mass or less, still more preferably 85% by mass or less with respect to the whole bioavailability enhancer.

[0051] When a bioavailability enhancer is orally administered to a human, the dosage of the transesterified oil composition can be appropriately determined based on the recipient's age, health condition, duration of administration, and frequency of administration. For a 60 kg adult, the transesterified oil composition can be administered so that they can ingest, for example, 100 to 25,000 mg of C13-C15 fatty acids per day, preferably 200 to 20,000 mg, more preferably 300 to 15,000 mg, even more preferably 500 to 10,000 mg, even more preferably 600 to 5,000 mg, and even more preferably 700 to 2,000 mg.

[0052] Furthermore, the bioavailability enhancer may contain components other than the transesterified oil composition. These components may include, for example, those commonly used as additives in supplements. More specifically, depending on the form of the bioavailability enhancer, it is possible to add general-purpose excipients, disintegrants, binders, lubricants, vitamins, xanthine derivatives, amino acids, pH adjusters, cooling agents, suspending agents, viscosity enhancers, solubilizers, antioxidants, coating agents, plasticizers, surfactants, water, alcohols, water-soluble polymers, sweeteners, flavoring agents, acidulants, fragrances, colorants, etc., within a qualitative and quantitative range that does not impair the effects of the invention.

[0053] (Methods for improving the absorption and bioavailability of C13-C15 fatty acids) In this embodiment, the method for improving the absorption of C13-C15 fatty acids includes the step of ingesting the transesterified oil composition obtained by the manufacturing method in this embodiment. The method for improving the bioavailability of C13-C15 fatty acids also includes the step of ingesting the transesterified oil composition obtained by the manufacturing method in this embodiment. In these methods, the target is specifically an animal, and more specifically a mammal. Examples of mammals include humans and non-human mammals. Examples of humans include healthy individuals aged 20 years or older. Examples of non-human mammals include livestock such as cattle, pigs, chickens, sheep, and horses, and pets such as dogs and cats.

[0054] Methods for administering the transesterified oil composition to the target include, for example, oral administration; transdermal administration such as topical application; inhalation; and injection such as intramuscular injection. The number of times the transesterified oil composition is administered per day may be, for example, 1 to 3 times.

[0055] The embodiments of the present invention have been described above, but these are examples of the present invention, and various other configurations can be adopted. Reference embodiments are listed below. 1. A method for producing a transesterified fat composition (excluding fats for hard butter and puff pastry margarine), comprising the step of transesterifying a raw oil containing a triglyceride composed of fatty acids having 13 to 15 carbon atoms and a fat other than the triglyceride to obtain a transesterified fat composition, wherein the transesterified fat composition contains 12% by mass or more and less than 100% by mass of fatty acids having 13 to 15 carbon atoms in the total fatty acids. 2. The method according to 1, wherein the fat other than the triglyceride is a vegetable oil. 3. The method according to 1, wherein the triglyceride composed of fatty acids having 13 to 15 carbon atoms is glyceryl tritetradecanoate. 4. The method according to 1, wherein the content of C20:5 fatty acids in the total fatty acids of the transesterified fat composition is 20% by mass or less. 1. The manufacturing method described in 1. 5. The manufacturing method described in 1., wherein the transesterification in the step of obtaining the transesterified oil composition is random transesterification. 6. The manufacturing method described in 1., which is a method for producing a transesterified oil composition for supplements. 7. The manufacturing method described in 1., which is a method for producing a transesterified oil composition for use as a bioavailability enhancer for fatty acids having 13 to 15 carbon atoms. 8. A method for producing an oil composition, comprising the step of obtaining a transesterified oil composition by the manufacturing method of a transesterified oil composition described in any one of 1 to 7. 9. The manufacturing method described in 8., further comprising the step of mixing the transesterified oil composition with an oil other than the transesterified oil composition. 10. A method for improving the absorption of fatty acids having 13 to 15 carbon atoms, comprising the step of having an animal ingest a transesterified oil composition produced by the manufacturing method described in any one of 1 to 7. 11. 1 to 7. A method for improving the bioavailability of a fatty acid having 13 to 15 carbon atoms, comprising the step of having an animal ingest a transesterified oil composition produced by any one of the manufacturing methods described.12. A bioavailability enhancer comprising, as an active ingredient, a transesterified oil composition made from triglycerides composed of fatty acids having 13 to 15 carbon atoms and oils other than the triglycerides as raw materials, wherein the transesterified oil composition contains 12% by mass or more and less than 100% by mass of fatty acids having 13 to 15 carbon atoms in the total fatty acids. 13. The bioavailability enhancer according to 12., which is an oral composition.

[0056] The embodiment will be described in detail below with reference to examples, but this embodiment is not limited to these examples.

[0057] (Raw Materials) The main raw materials used in the following example are listed below. Rapeseed oil: AJINOMOTO Smooth Canola Oil, manufactured by J-Oil Mills (4.1% by mass of fatty acids with 16 carbon atoms in the total fatty acids) Free myristic acid: manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Trimyristic acid: manufactured by Tokyo Chemical Industries, Ltd.

[0058] (Production Example 1) In this example, glyceryl tritetradecanoate (trimyristine) was obtained by the following procedure. 89.7 parts by mass of myristic acid (tetradecanoic acid) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 10.3 parts by mass of glycerin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed, and 0.1 parts by mass of sodium hydroxide was added as a catalyst. The mixture was stirred at 220°C and atmospheric pressure for 240 minutes while blowing in nitrogen to carry out the ester synthesis reaction. After the ester synthesis reaction, an aqueous sodium hydroxide solution was added to deacidify the mixture and remove the unreacted tetradecanoic acid. After deacidification, the mixture was decolorized using activated clay and then deodorized to obtain glyceryl tritetradecanoate. The obtained glyceryl tritetradecanoate was used in Production Example 2.

[0059] (Manufacturing Example 2) In this example, the transesterified oils of Examples 1 and 2 were obtained by the following procedure. To 100 parts by mass of a mixed oil prepared by mixing each oil and fat according to the "Transesterified Oil Formulation" described in Table 1, 0.3 parts by mass of sodium methoxide was added as a catalyst, and a random transesterification reaction was carried out for 60 minutes with stirring at 80°C and a vacuum of 2.0 kPa or less. After the random transesterification reaction, the catalyst was removed by washing with water. After washing with water, decolorization treatment was performed using activated clay, and then deodorization treatment was performed to obtain each transesterified oil. The fatty acid composition of the obtained transesterified oils is shown in Table 1. The fatty acid composition of the test substance for each comparative example is also shown in Table 1. The fatty acid composition was analyzed by the following method.

[0060] (Analysis Method for Fatty Acid Composition) Each test substance listed in Table 1 was converted to fatty acid methyl ester using the boron trifluoride methanol method. Then, the fatty acid composition was analyzed by gas chromatography (GC) under the following conditions, and the content (mass %) of each fatty acid in the total fatty acid composition was calculated. The results are shown in Table 1. In the fatty acid composition in the table, the numbers outside parentheses indicate the content expressed as mass % calculated using the molecular weight of the fatty acid from the mass % derived from the area value obtained by GC analysis, while the numbers inside parentheses indicate the content expressed as mass % calculated from the area value obtained by GC analysis. Also, in the table, for example, "C14:0" represents a fatty acid with 14 carbon atoms and 0 unsaturated bonds, and "C18:1" represents a fatty acid with 18 carbon atoms and 1 unsaturated bond. In addition, "-" in the fatty acid composition of Table 1 indicates 0.5 mass % or less. • GC instrument: Product name GC2010 (manufactured by Shimadzu Corporation) • Column: DB-23 (30m x 0.25mm x 0.25μm) (manufactured by Agilent Technologies) • Inlet temperature: 230℃ • Carrier gas: Helium (45.4 mL / min) • Split ratio: 50:1 • Column temperature: 80℃ 2 min → (35℃ / min) → 160℃ → (2℃ / min) → 230℃ 8 min • Detector: Flame ion detector (240℃)

[0061]

[0062] (Examples 1 and 2 and Comparative Examples 1-4) The absorption efficiency of C13-C15 fatty acids in plasma was evaluated when the test substance for each example was orally administered to rats. The formulations of the test substances in each example are shown in Table 1.

[0063] (Test Method) 1. Animals Used Animal species: Rat Strain: Crl: CD (SD) Supplier: Jackson Laboratory Japan Sex: Male Age: 8 years old at arrival, 9 weeks old at administration Number of animals: 8 animals / group × 6 groups

[0064] 2. Method Animals brought in ↓ Acclimatization for 6 or 7 days (Solid feed for small animals MF, manufactured by Oriental Yeast Co., Ltd. Comparative Examples 1, 2, and Example 1 were acclimatized for 6 days, Comparative Examples 3, 4, and Example 2 were acclimatized for 7 days) ↓ Grouping by body weight ↓ Feed collected 17 hours before administration and fasting ↓ Oral administration of suspension ↓ Blood samples taken 0, 1, 2, 3, and 4 hours after administration

[0065] 2-1 Preparation of Test Substances and Administration The dispersion of the test substance was prepared on the day of administration by the following method. Solvent: 0.5 w / v% methylcellulose 400 solution, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Final concentration: 300 mg / mL The test substance (Table 1) and solvent for each example were sonicated using a Bioremo ultrasonic homogenizer (SONICSTAR 85, manufactured by AS ONE Corporation). After sonication, the samples were stored in a 40°C constant temperature bath until administration. Before administration to each individual, sonication was performed for 20 seconds, and the sample was administered at 2250 mg / 7.5 mL / kg B.W.

[0066] 2-2 Blood Collection Method Unanesthetized animals were restrained manually, and after wiping the neck area with an alcohol swab, approximately 0.2 mL of blood was collected from the jugular vein using a syringe and needle treated with heparin sodium. The collected blood was transferred to a 1.5 mL transparent polypropylene tube and stored under ice-cold, light-shielded conditions until plasma separation. Centrifugation was performed at 10000 × g, 5 min, and 4°C (Model 3740, Kubota Manufacturing Co., Ltd.), and at least 100 μL of plasma was dispensed into one 1.5 mL transparent polypropylene tube and rapidly frozen with dry ice. The tubes were then stored frozen in a freezer set to -80°C (acceptable range -60°C or below) until analysis.

[0067] 3. Method for analyzing plasma fatty acids A commercially available fatty acid methylation kit (Nacalai Tesque) was used to perform methyl esterification according to the following procedure. 15 mL centrifuge tube ↓ 25 μL plasma ↓ 0.5 mL Solution A (solvent) ↓ vortex ↓ 37°C 30 min ↓ 0.5 mL Solution B (reaction solution) ↓ vortex ↓ 37°C 1 h ↓ 0.5 mL Solution C (stop solution) ↓ 37°C 20 min ↓ 2 mL Hexane (0.1 mg / mL methyl heptadecanate) ↓ 3000 rpm, 5 min ↓ Upper layer ↓ 1 mL distilled water ↓ vortex ↓ PVDF filter ↓ Upper layer (GC) The obtained upper layer was analyzed by GC according to the following method. • GC system: Product name GC2010 (manufactured by Shimadzu Corporation) • Column: DB-23 (30m x 0.25mm x 0.25μm) (manufactured by Agilent Technologies) • Inlet temperature: 230°C • Carrier gas: Helium (45.4 mL / min) • Splitless column temperature: 80°C 2 min → (35°C / min) → 160°C → (2°C / min) → 230°C 8 min • Detector: Flame ion detector (240°C)

[0068] (Analysis Method) The area values ​​of myristic acid and heptadecanoic acid, used as an internal standard, were calculated from the chromatograms obtained by GC analysis. The plasma myristic acid concentration was calculated using the following formula: Plasma myristic acid concentration = (myristic acid area value) * (heptadecanoic acid methyl concentration (mg / mL)) * (extract volume (mL)) / (heptadecanoic acid area value) * (plasma volume used for analysis (dL)) In Figure 2, "p" indicates the result of multiple comparison testing by Tukey-Kramer. †† (p < 0.01): vs Comparative Example 3 * (p < 0.05): vs Comparative Example 4 The plasma myristic acid concentrations at 0, 1, 2, 3, and 4 hours in each example are shown in Table 2, Figure 1, and Figure 2. Furthermore, based on these results, the area under the curve (AUC) of myristic acid blood concentration in each case was calculated using the following formula: AUC = ((0h concentration (mg / dL) + 1h concentration (mg / dL)) * 1 (h) / 2) + ((1h concentration (mg / dL) + 2h concentration (mg / dL)) * 1 (h) / 2) + ((2h concentration (mg / dL) + 3h concentration (mg / dL)) * 1 (h) / 2) + ((3h concentration (mg / dL) + 4h concentration (mg / dL)) * 1 (h) / 2) - (0h concentration (mg / dL) * 4 (h)) The results are shown in Table 2, as well as in Figures 3 and 4. In Figure 4, "p" indicates the results of multiple comparison testing using the Tukey-Kramer method. Note that the myristic acid concentration and AUC values ​​in the plasma shown in Table 2 are average values ​​(n=8).

[0069]

[0070] As shown in Table 2 and Figures 1 to 4, in Examples 1 and 2, where transesterified oil was used as the test substance, the concentration of C13-C15 fatty acids in plasma was effectively increased compared to Comparative Examples 1 to 4, where free myristic acid or trimyristic acid was used as the test substance.

[0071] (Examples 3, 4 and Comparative Examples 5-7) The excretion rate of myristic acid in the feces was evaluated when the test substance of each example was orally administered (ad libitum feeding) to rats. The formulation of the test substance in each example is shown in Table 4. Transesterified oils A and B in Examples 3 and 4 were obtained according to the procedure described in (Production Example 2) above, in accordance with the "Transesterified Oil Formulation" described in Table 3. The fatty acid compositions of the obtained transesterified oils A and B are shown in Table 3. For Example 4, a fat and oil composition was obtained by mixing rapeseed oil with the obtained transesterified oil B. The fatty acid composition of the obtained fat and oil is shown in Table 4. Table 4 also shows the fatty acid composition of the test substance in each comparative example. The analysis of the fatty acid composition was performed according to (Method of Analyzing Fatty Acid Composition) above. The values ​​of the fatty acid composition in Tables 3 and 4 represent the content expressed as mass percent calculated using the molecular weight of the fatty acid from the mass percent derived from the area value obtained by GC analysis. In addition, "-" in the fatty acid composition in the table indicates 0.5 mass percent or less.

[0072]

[0073]

[0074] (Test Method) 1. Animals Used Animal species: Rat Strain: Crl: CD (SD) Supplier: Jackson Laboratory Japan Sex: Male Age: 8 years old at arrival, 9 weeks old at the start of administration Number of animals: 48 (8 animals / group x 6 groups)

[0075] 2. Method Animal introduction ↓ 6-day acclimatization (solid feed MF for small animals, manufactured by Oriental Yeast Co., Ltd.) ↓ 4-day acclimatization (acclimatization diet (AIN-76 modified feed)) ↓ Grouping by body weight ↓ 10-day administration of test diet (oral ad libitum) The start date of test diet administration was designated as Day 0, and measurements were taken as follows: Body weight measurement: 5 times on Day -10, -1, 0, 5, and 10 Food intake measurement: 4 periods each for Day 0 to Day 3, Day 3 to Day 5, Day 5 to Day 7, and Day 7 to Day 10 Fecal collection and weight measurement: 2 periods each for Day 3 to Day 7 and Day 7 to Day 10 Based on the obtained food intake and the composition of the test diet described in Table 6 below, the amount of fat intake (g) was calculated.

[0076] 2-1. Preparation of acclimatization diet and test diet. An acclimatization diet (powdered feed) was prepared by combining each component according to the formulations listed in Table 5 below. A test diet (powdered feed) was also prepared by combining each component according to the formulations listed in Table 6 below. In Table 6, for "oils and fats*", the test substances listed in Table 4 were used for each example.

[0077]

[0078]

[0079] 2-2. Fecal Collection Method The cages were changed on the first day of collection, and all feces in the cages were collected on the last day of collection. The collected feces were placed in 50 mL tubes (CORNING, No. 430829) with tare weight already measured, and after measuring the fecal weight (g), they were frozen and stored in a freezer set to -80°C (acceptable range -60°C or below) until analysis (2-3. Fecal Lipid Extraction).

[0080] 2-3. Method for Extracting Fecal Lipids Feces ↓ Freeze-dry at -20°C for 24 hours ↓ Crushed ↓ 1 g Centrifuge tube ↓ 3 mL concentrated hydrochloric acid ↓ 3 mL distilled water ↓ 50°C for 30 min ↓ Room temperature ↓ 40 mL diethyl ether (0.25 mg / mL methyl tricosanate) ↓ 1 min Voltex ↓ 1000 × g for 10 min centrifugation ↓ 20 mL supernatant Round-bottom flask ↓ Dry In each example, the weight of lipids (g) in 1 g of feces was measured. In addition, the fatty acid composition of the fecal lipids obtained in each example was measured according to the above (Method for Analyzing Fatty Acid Composition), except that the GC instrument was changed to a GC2030 (Shimadzu Corporation). From the obtained fatty acid composition results, the weight of myristic acid (mg / g) per 1 g of fecal lipid was calculated.

[0081] (Calculation of Myristic Acid Excretion Rate) The myristic acid excretion rate (%) was calculated from the obtained fecal weight (g), the myristic acid weight per gram of fecal lipid (mg / g), the lipid weight per gram of feces (g / g), the myristic acid weight per gram of fat in the test food (mg / g), and the fat intake (g) according to the following formula: Myristic acid excretion rate (%) = (Myristic acid weight per gram of fecal lipid (mg / g) × Lipid weight per gram of feces (g / g) × Fecal weight (g)) / (Myristic acid weight per gram of fat in the test food (mg / g) × Fat intake (g)) × 100 The results are shown in Table 7, and in Figures 5 and 6. In Figures 5 and 6, "p" indicates the results of multiple comparison tests using the Tukey-Kramer method. The values ​​for each item in Table 7 are mean values ​​(n=8).

[0082]

[0083] From Table 7 and Figure 5, in Example 3, where transesterified oil was used as the test substance, the myristic acid excretion rate was lower compared to Comparative Examples 5 and 6, where free myristic acid or trimyristic acid was used as the test substance. From Table 7 and Figure 6, in Example 4, where an oil and fat composition containing transesterified oil was used as the test substance, the myristic acid excretion rate was lower compared to Comparative Example 7, where free myristic acid was used as the test substance. Here, if we define the intake of myristic acid as 100 (%), and myristic acid intake (100%) - myristic acid excretion rate (%) = myristic acid absorption rate (%), then it can be said that the absorption of myristic acid was improved in Example 3 compared to Comparative Examples 5 and 6, and in Example 4 compared to Comparative Example 7.

[0084] This application claims priority based on Japanese Patent Application No. 2024-173844, filed on 2 October 2024, and incorporates all of its disclosures herein.

Claims

1. A method for producing a transesterified fat composition (excluding fats for hard butter and puff pastry margarine), comprising the step of transesterifying a raw fat containing a triglyceride composed of fatty acids having 13 to 15 carbon atoms and a fat other than the triglyceride to obtain a transesterified fat composition, wherein the transesterified fat composition contains 3% by mass or more and less than 100% by mass of fatty acids having 13 to 15 carbon atoms in its total fatty acid content.

2. The manufacturing method according to claim 1, wherein the oils and fats other than triglycerides are vegetable oils and fats.

3. The manufacturing method according to claim 1, wherein the triglyceride, which is composed of a fatty acid having 13 or more carbon atoms and 15 or less carbon atoms, is glyceryl tritetradecanoate.

4. The manufacturing method according to claim 1, wherein the content of C20:5 fatty acids in the total fatty acids of the transesterified oil composition is 20% by mass or less.

5. The manufacturing method according to claim 1, wherein the transesterification in the step of obtaining the transesterified oil composition is random transesterification.

6. The manufacturing method according to claim 1, which is a method for producing an transesterified oil composition for supplements.

7. The manufacturing method according to claim 1, which is a method for producing a transesterified oil composition used as a bioavailability enhancer for fatty acids having 13 or more carbon atoms and 15 or less carbon atoms.

8. A method for producing an oil and fat composition, comprising the step of obtaining a transesterified oil and fat composition by the method for producing a transesterified oil and fat composition described in any one of claims 1 to 7.

9. The manufacturing method according to claim 8, further comprising the step of mixing the transesterified oil composition with an oil other than the transesterified oil composition.

10. A method for improving the absorption of fatty acids having 13 to 15 carbon atoms, comprising the step of having an animal ingest a transesterified oil composition produced by the manufacturing method described in any one of claims 1 to 7.

11. A method for improving the bioavailability of a fatty acid having 13 to 15 carbon atoms, comprising the step of having an animal ingest a transesterified oil composition produced by the manufacturing method described in any one of claims 1 to 7.

12. A bioavailability enhancer comprising, as an active ingredient, a transesterified oil composition made from triglycerides composed of fatty acids having 13 to 15 carbon atoms and oils other than the triglycerides as raw materials, wherein the transesterified oil composition contains 3% by mass or more and less than 100% by mass of fatty acids having 13 to 15 carbon atoms in its total fatty acid content.

13. The bioavailability enhancer according to claim 12, which is an oral composition.

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